Chemoselective Synthesis of Polysubstituted Pyridines From Heteroaryl Fluorosulfates

Chemistry. 2016 Apr 11;22(16):5692-7. doi: 10.1002/chem.201600167. Epub 2016 Mar 15.

Abstract

A selection of heteroaryl fluorosulfates were readily synthesized using commercial SO2F2 gas. These substrates are highly efficient coupling partners in the Suzuki reaction. Through judicious selection of Pd catalysts the fluorosulfate functionality is differentiated from bromide and chloride; the order of reactivity being: -Br> -OSO2 F> -Cl. Exploiting this trend allowed the stepwise chemoselective synthesis of a number of polysubstituted pyridines, including the drug Etoricoxib.

Keywords: Suzuki reaction; chemoselectivity; cross-coupling reactions; fluorosulfates; palladium; polysubstituted pyridine.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Etoricoxib
  • Molecular Structure
  • Palladium / chemistry*
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Sulfones / chemical synthesis*
  • Sulfones / chemistry

Substances

  • Pyridines
  • Sulfones
  • Palladium
  • Etoricoxib